There's something about anniversaries that can make a person feel especially reflective. Leading up to the 10th anniversary reissue of his debut album, Lights Out Paris—which is out on vinyl for the first time today—I wondered if Sims might be in the mood to think back to his beginnings of working with Doomtree and unpack some of the progress he's made as an artist (and a person) since that album came out. It turns out he was in just the right headspace for a deep-diving conversation about the past, present, and future of his journey and his career.

After chatting with David Campbell for this week's Local Show, Sims and I sat down at Black Sheep Pizza and split a Farmer's Market Salad as we chatted about his growth as a writer, his strategies for managing anxiety and depression, and his complicated relationship with his fans. Because of the length of our conversation, I'm presenting this interview in two parts. Read the second half here.

Andrea Swensson: In your interview for The Local Show this week, I thought it was interesting when you mentioned that, as a writer, you’re not trying to pack in as many lyrics as you were in your spitfire early days. Can you talk more about how you’ve evolved your writing style?

Sims: That kind of works two ways. Sonically, it’s allowing certain words to resonate a little more, so you leave a little more space in each measure of the beat of the song, and let things catch a little bit more instead of bombarding people with a rapid-fire approach. And that doesn’t mean that I won’t go fast from time to time, and try to get as patterny and quick as I can, but I try to space out a little bit more. I try to give it some room to stand, and some room to breathe.

And then in the actual language, I'm trying to take something that’s complicated, and boil it down into a simple thing. Taking a complicated idea, making is at easily relatable and translatable, and then still making it eloquent is a really challenging thing to do. I think that’s every writer’s challenge: to boil a hugely interesting idea down to something that’s easily conveyable, and then [adding] layers to it so there’s stuff to unpack. Part of that is using words that are more readily identifiable. Instead of trying to impress people with a vocabulary, just do it simply, and try to get to the root of it. Using a scalpel instead of a hammer. So that’s a challenge.

It’s hard, right now, trying to figure out what the f*ck to write about—you know what I mean? How do you come up with these new ideas? I always talk to artists about “What are you making? What are you writing about right now? What are you thinking about right now?" Because there’s a whole world of stuff to talk about, but trying to communicate things that we have in common that we’re thinking about, that you’re also thinking about, that I’m also thinking about, he or she’s also thinking about, is a good place to start.

Do you feel like you’re choosing between describing what you’re specifically experiencing, or painting a broader picture of what society is dealing with?

Yeah. I feel like they’re interchangeable, and I’ve been trying to write less about the world at large and more about my world. And sometimes I find that awesome, and sometimes I find that too self-indulgent and small. Sometimes it’s the world stuff that’s really interesting to me. I’m not really big on love songs, which is strange. A lot of people love love songs. It’s the most relatable topic, probably, because everyone goes through that in some capacity. And yet it’s not my thing. I don’t like listening to them, I don’t really like writing them. So you’re left with a different avenue of approaches.

You mentioned a tendency to want to show off your vocabulary in your writing. There’s this element of bravado at the core of hip-hop culture. Do you feel like, as someone who approaches things from an intellectual standpoint, that you have to have an intellectual bravado?

Absolutely. When boiled down, ego is a huge driver for almost anything that anybody ever does. And you can really boil all that down to sex, and the sex drive. So pulling it all back from that, yeah. I think so. I think a lot of people take a lot of pride in being smart and genius, and they want to be recognized for being smart and genius. I don’t think there’s anything wrong with that. There’s some rappers that I like right now who are smart, but they are too heavy-handed in their smart.

But there’s one guy in particular who’s so genius in how smart he is and makes his message really simple: Open Mike Eagle. He is a perfect example of unpackable lyrics. Because he’s got a lot to say, and he does it in a condensed space. And some of it’s humorous and some of it’s not, and some of it’s really sad and dark, but he’ll hit you again. He’s like a great comedian in that way. Like George Carlin would say something really funny, and then say something super devastating, and then follow it up with something really funny. And there’s a great line of communication in that.

I think Aesop Rock is also amazing at that. He’s so smart. He’s so verbose that it’s hard to say he’s understated, but if you listen to his songs over a long enough span of time, he’s changed a little bit and revealed a little more about himself, but he’s still pretty coded and private in that way. And I don’t think he’s got a lot to prove. I don’t think he’s trying to sound smart. That’s just the way he thinks and writes. He’s actually on Mike’s podcast this week.

I just bookmarked that—they talk about anxiety and depression, right?

Yeah. I mean, Mike talks about that a lot. When I was on Mike’s podcast we talked about that too. Mike’s great. He’s really interested in that kind of stuff.

Well, it seems like that’s at the core of a lot of people’s creative process.

It’s unfortunate but it’s true. I actually—I struggle with it a lot. This year especially, and the last couple of years. After [Sims' wife] Sarah got her transplant and everything went so poorly, I got so depressed from August 2012 to like the beginning of last year, pretty much, when I went to Europe. That was a really dark time in my life. It was a year and a half of totally dark depression. Things were bad. And I’ve still really struggled with it since. This spring I hit a really bad depression. When I got off the All Hands tour, and should be riding high—like that was the most successful time ever. I got home with a head of steam, like "I’m going to write this record right now, I’m really excited to write this record." And I can’t do it. I keep coming up with excuses why I can’t do stuff. Like I can’t get out of this weird hole, you know? Yeah, depression’s a weird thing. But I just went on meds this week.

I literally just went to the psychiatrist and got a prescription today.

Did you really? I’m on my third day. I’ve literally tried everything. Like I’ve started exercising like crazy, I started changing my diet like crazy, I quit drinking for two months, I stopped smoking weed. And nothing was really helping. You know? It helps, all of it, but there’s still a thing I can’t pass. There’s like a block. So I’m trying to figure that sh*t out. I tried talk therapy, too, but it didn’t work for me, as well. I think I’m really good at rationalizing to someone else. I’m an excellent bullsh*tter.

Me too. I had a breakthrough recently. I’ve had a tough year, and I was talking to my doctor and I was like, “My life is falling apart!” And he was like, "Actually, no it’s not. And the more you say that, the more it’s going to feel like it is. You’re fine, you’re dealing with stuff. It’s going to be fine." And I was like, "Oh, ok."

It’s weird, it can like manifest, right? I’m really, really mean to myself. Like I don’t believe in myself at all. I’m super mean to myself and I have this weird duality of supreme confidence in my ability—I really, truly believe I’m really good at what I do. And I think that I still have untapped potential, like there’s a well in there somewhere that I’m really trying to get to, and once I get to it, it’s going to be great. And I don’t know if I’m going to get to it by the time I die or not. And yet, there’s this other thing, this overriding deal that shuts that down, because I’m really mean to myself. And I think I suck. And I think I’m terrible. It’s that crippling self-doubt. Before a show I’m just—unless it’s a show with Doomtree, then I’m cool as a cucumber, it doesn’t matter, because I’m not really thinking about stuff, I’m just hanging out with my bros. But before a Sims show, I’m just this wreck. On tour, a Sims tour is a terrible time, it’s just this anxiety.

Are you alone on tour, or do you have a DJ?

Yeah, I’ll go with people. But it’s not the same, I don’t know why. There’s no one to deflect onto. I’ve been waking up in the middle of the night with, I guess you’d call it a negative thought loop. Like I wake up in the middle of the night trapped in this negativity. Waking myself up out of a dead sleep with these terrible thoughts, and I sit up for like two hours. I was telling Sarah about that and she was like, dude, you need to just try some meds. Because that's not supposed to happen.

Do you feel comfortable writing about that kind of stuff?

Yeah, I do, but it’s not cool. When I was 20, I was way more down with doing braggadocio stuff, because I felt way more confident and cocksure and cocky. And now I’m 32, it’s different. I don’t really believe all that sh*t anymore, and I don’t really believe anyone that says that stuff. I think it’s great when kids are doing that—I love when kids are bragging. It’s part of hip-hop, it makes me feel good in a way. But it’s hard to write about that stuff. One of the hard things about making rap music is, the golden era of rap music is over. The era of underground rap music is over. It’ll be around and come back in some capacity, but what you have to do is make your stuff sound interesting to 20-year-olds. I mean, there’s 30-year-old listeners, but they’re not coming to concerts. 40-year-olds are not coming to concerts. They’re coming to some, but they have kids. Jobs. Responsibilities. So you have to somehow stay relevant and interesting to kids, and relatable to kids, and so to talk about depression—I think you have to sprinkle those things in. Because by and large, you’ve still got to sound cool. And you’ve still got to make cool music, that sounds cool.

The other thing, too, is that when I make songs about depression, they’re tough, and they’re about depression. So somehow, if you can make something that’s enjoyable to listen to and sprinkle that stuff in, that’s maybe a good way to approach it. So I’m trying to think of how to make a song that you can play in the car, and to be fully honest, that you could play on a commercial too if you wanted, and still make it heady and sharp and urgent, and all those things that it needs to be. And urgency is a weird thing. When you’re 30, coming up with urgent matters is different. The world isn’t as desperate as it was when I was 20. That was a more desperate viewpoint, you know? And part of that’s living off $400 a month. Part of that is struggling with coping with the reality of your situation—like, this is your country, it operates like this. This is how people operate. People can be sh*tty. And then struggling with the fact that, later, that might just be ok. Because people are just people, and they do their best. It’s not so black and white. Things become a lot hazier. The more you learn, the less you understand about stuff.

More from Sims: read about his thoughts on Macklemore, Kendrick, personal brands, and Doomtree's unexpectedly complicated relationship with its fans in part 2.